Blowing out her fiftieth birthday candle, Cuba is smiling ironically at the surrounding capitalist world driven in desperation to the ultimate socialist measures – nationalisation of banks and other huge industries. For decisions no less drastic, and for no less a reason than self-protection against the vanity of global conglomerates, the revolutionary Castro government took a series of similar measures in 1959, aimed at promoting Cuban self-reliance and ousting American and international ownership of Cuban industry.

These early steps, which were aimed at creating a fairer distribution of wealth and an economy driven for Cubans by Cubans, formed part of a new moral and ethical stance directed at shifting imperial power and casting out undue American influence which left ordinary Cubans impoverished, hungry and reduced to second-class citizens in their own country.

No examination of the success of Castro can be complete without recalling the brutality and excesses of the previous Batista government, a dictatorship which had been supported by the US until it was clear that Batista, whose mixed race meant that he himself was not allowed to enter some of the most exclusive social clubs in Havana, was about to be ousted.

Today, Cuba stands alone, determined to mark her progress through fiestas in every town, yet distinctly isolated by the respective failures of socialist and communist governments throughout Latin America and eastern Europe. Her lifeline, the Soviet Union, has melted away in an increasingly disparate pile of roubles, and her archenemy, the US, is bubbling in an economic froth of its own making, forcing its own government to resort to ever-larger state control. As this proud and dynamic country marks 50 years of revolutionary history, is her wry smile justified?

There are no easy answers to the Cuban conundrum. Within the first days of rolling into Havana, bearded and brandishing the new ideology of Cuba Libre, Castro publicly stated that he envisaged holding democratic elections within 18 months. Fifty years later, the country remains a tightly controlled one-party state. Freedom of expression remains considerably constrained, and political opponents over the years have found themselves glaring at the insides of prisons.

Castro would argue, and has argued, that he has had no choice in retaining such a tight grip over the country since his island is not only perilously close to Miami, but swims among the same political sharks that have overturned all or most democratically elected socialist governments in central and Latin America. One cannot relegate to the scrapheap some of the earliest formative impressions of American power upon both him and Ernesto Che Guevara in the second half of the 20th century – the brutal American intervention in Guatemala came to be repeated across the continent, with Chile and Nicaragua remaining high on the democratic socialist casualty lists.

The barely masked interventions from the CIA and successive American governments have led to mass casualties and brutal military repression in every country where their presence has been felt, something Cuba has managed to avoid: Cuba's own flotilla of badly constructed rowing boats fleeing the island through its self-named special period in the 1990s, a time when Cubans found themselves again without food, clothes or soap after the Soviet Union collapse removed a huge national income, led to an evacuation of sorts, however, in any event.

Castro may have underestimated the ability of his own people to vote in favour of a socialist government, it is true, but given the Ahmed Chalabi card as just one recent example of American intervention in "democracy" in Iraq, the idea that America might have left Cuba alone to vote and elect a socialist government is absurd. The freedom to choose must be absolute, but the recent economic crisis must demonstrate to us in the so-called democratic west that our own choices are extremely limited indeed. In England, for example, there is no real choice between Labour and Conservative beyond a beauty pageant and a gravy train. There is no real choice for local rather than global taste while our high streets, currently crashing around our luxury plates and babywear, are taken over by faceless enterprises run anywhere but Britain.

Propaganda, too, is no more than the tool of the powerful to make the people look in their direction. Street signs everywhere in Cuba now may proclaim the victory of the revolution, as the state newspaper Granma proclaims the ideology and successes of the Castro brothers, but is there any less harm caused to a nation who sits gripped on the morning and evening rush hour by a dumbed-down version of select pieces of news, not to forget the celebrity gossip, by the makers of Metro, London Lite or any of the other free newspapers handed out by the thousands across urban Britain, Europe or the US. A better Orwellian interpretation of freedom there may not be. Choice is a much-maligned word, by both the Bush and Blair governments, and in the society that has been created and shaped in their parties and in their wakes.

The world's largest democracy, India, has much to hold up in pride since its independence from Britain, but equally, with hundreds of millions of people subsisting at below the poverty line, living in inhumane conditions without access to clean water, sanitation or education, the right to vote is a mere formality to be bought off by sacks of rice and lentils provided by power-hungry politicians who can play on local or religious sensibilities with a handful of grain.

The so-called first-generation human rights, those such as the right to freedom of expression or association, are meaningless without accompanying rights to eat, work and have a roof over our heads. Cuba's socialist government has stressed these rights, known in the west as second- and third-generation human rights, over the first. Can we easily dismiss such logic? Or so easily consider our own society flawlessly able to dictate to others how they should prioritise?

None of this is to denigrate or decry the fundamental importance of the right to choose, and the right to express ourselves freely. Had Castro felt sufficiently confident to allow his people to choose, the world may have been surprised by the pride and aspirations many ordinary Cubans show in their country's achievements and equality. It would have been fascinating to have seen whether Guevara, had he remained as part of the Cuban cause, would have pressed elections upon his friend and comrade, and whether his own overwhelmingly popular personality could have been enough to stand up and fight any concerted attempt by its capitalist neighbour to undermine and vandalise free and fair elections.

Many of the teenagers I have spoken with in Havana would wear Guevara T-shirts at the same time as Nike trainers, if only they could have access to the latter. Cuba has so much to be proud about today, not least its ability to meet basic needs of most of its population, but economic and political choices made in the past continue to haunt its long-suffering people, particularly those in the countryside without access to the much-needed dollar, which already has divided this country into haves and have-nots.

While the enduring legacy of both Castro and Guevara's revolution may be that, for just a while, they made everything seem possible, the biggest failing of the revolution today may be the eternal lack of possibility in Cuba, suffocating the island's exuberant joy. Would the lifting of the blockade and free elections monitored by an independent UN body be sufficient to give hope, choice and socialism to the current generations of Cubans who have known economic disaster as their status quo?

Barack Obama's new administration is about to take over across the straits. If ever Castro, senior or junior, wanted to test how successful the revolution had been, perhaps the answer no longer lies in quoting understandably impressive statistics about free education, healthcare and life expectancy. It is unlikely that Fidel will emerge in the Plaza de La Revolucion in Havana on New Years Day championing a third way for democratic socialism. All bets are off as to whether he even will address the expected crowds. Still, perhaps the revolutionary government could begin a new revolution in Cuba in 2009 and recognise finally that it is time for its people to choose.